The Rudder

Right now, as I write this, an iPod is playing.

Not through Bluetooth, not casting to a TV, not waiting on a technological “handshake” between two sources that fails twice before it connects. A headphone cable runs out of the jack and straight into a Tivoli Audio Model Two, and the music fills my home office because two physical objects are touching. That’s the whole signal chain. Nothing in the cloud gets to inject an opinion about it.

The iPod is a sixth generation “classic”, gutted and rebuilt. A terabyte of storage on a microSD card where the spinning drive used to be. A logic board that runs Rockbox instead of anything Apple ever shipped. A battery that lasts for days. A dark charcoal felt sleeve some kind soul made to order on Etsy. All in, it ran me about $350, and yes, I know exactly how many months of streaming that buys. I did the math so you don’t have to. I’d ask Star-Lord for a second opinion, but he seems happy with his Walkman, a similar setup.

There’s no rock in Rockbox, by the way. Blues? Plenty. But no rock songs. The name is an inside joke about what I use it for. My inner nerd smirks every time I see the logo flash during its four-second bootup.

Here’s the part that makes people twitch. To play a specific song, I have to work for it. I want Jonn Serrie’s “Gentle: The Night,” so I put my thumb on the wheel and start spinning, clockwise and counter, drilling down through the library until I land on it. Thirty seconds, maybe. Building an actual playlist means holding buttons in sequences that reactivate a trauma I first suffered typing text messages on a numeric keypad, back when the letter C cost you three presses of the 2 button. In 2026 I could summon any song on earth in under a second by talking to a piece of glass. Instead I spin a wheel like it’s 2006. I dig it.

Thirty seconds of thumbing the wheel toward Jonn Serrie is thirty seconds of choosing Jonn Serrie on purpose with intent. The effort-of-thumbs is a small price to pay for my music listening experience. My thumb on that wheel is me voting for exactly what I meant to hear. Every time. The device rewards me as I sit with a whole album the way it was originally sequenced. It punishes impulsive playlist-hopping, which suits me fine, because I never liked playlists anyway.

The effort-of-thumbs comes with a tax, and I begrudgingly pay it with a laptop I’m embarrassed to own. Getting my high-quality FLAC music files onto the iPod means I have to boot a barebones Windows machine that exists for this one job and nothing else. I plug the iPod in by USB so I can copy an album over from my home file server, a Synology Network Attached Storage device. It takes time. I grumble the whole way through. That little laptop is the necessary friction for living off-cloud, and I pay it without complaint, although my teeth grit when several silly popup notifications slide out from the right side of the Windows desktop. The alternative is handing my music listening keys over to someone else.

This is where the skeptics come in, and there are many. My wife is a skeptic. My coworkers are skeptics. People who’ve never met me but subscribe to my newsletter are skeptics. Everyone has an opinion about how I should listen to music, and most of them would like me to hold their opinion for a while, the way you’d hand someone your plate to carry.

I understand the case against me. Any song, immediately. A nominal monthly fee for more music than I could finish in a lifetime. I get it. I just don’t want it, and it took me most of my life to be able to say that confidently. There was a decade where I would have cared what the room thought of my choices. The freedom to not care lives on the other side of that decade, and I earned the right to do my own thing.

So here’s the actual reason I continue to use my modded iPod, the one underneath the price and the friction and the wheel.

My musical tastes make no sense. I’ll play Vangelis into The KLF into Patrick O’Hearn, then swing straight into Five Finger Death Punch and Black Label Society without even thinking about it. There is no rudder an algorithm could ever deploy for my musical preferences at a given minute of the day. And that is the point. A recommendation engine needs me to be predictable. It needs to stick me into a hexagonal-shaped box it can sell against, and my listening life is an Icosagon. (Look it up, kids.) The iPod can hold the unpredictability because it doesn’t care who I am. It just plays the next thing my thumb found. The algorithm can’t deal, because taste that complex won’t resolve into a pattern.

So no, I don’t want the big company knowing what I like. But that’s the polite reason for my offline music device. The more important reason, the one I get loud and obnoxious about, is that the machine stopped watching and started steering, deciding what I should want next and calling it a service. Lately it’s injecting AI-generated tracks into the mix nobody asked for, just to keep the party going. That ain’t curation where I came from. That’s someone subversively taking control of the rudder while telling me I’m still sailing where I want to go.

Every time I press play on the iPod, I hear my music. Not a DJ in the cloud, not a model that claims to know me better than I know myself, not a synthetic song wearing a real one’s clothes. Just the album I chose, playing into a radio, on a device that asks nothing of me but a charge on Saturday night before I go to sleep.

More later...